Visible-Light-Induced Insertion of Siloxycarbene into Amide N-H Bonds: Synthesis of Carbinolamides from Acylsilanes and Amides

被引：0

作者：

Dharavath, Praveen ^{[1
,2
]}

Vaggu, Raju ^{[1
,2
]}

Manda, Rajesh ^{[1
]}

Gree, Rene ^{[3
]}

Das, Saibal ^{[1
,2
]}

机构：

[1] CSIR Indian Inst Chem Technol CSIR IICT, Dept Organ Synth & Proc Chem, Hyderabad 500007, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

[3] Univ Rennes, Inst Chem Sci Rennes, CNRS, UMR 6226, F-35000 Rennes, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2025年 / 90卷 / 04期

关键词：

CARBENE INSERTION; ARYL HALIDES; HETEROCYCLES; AMIDATION;

D O I：

10.1021/acs.joc.4c02818

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The insertion of carbene into secondary amide N-H bonds remains underexplored in organic synthesis. In this work, we discovered the visible-light-induced insertion of siloxycarbene into amide N-H bonds. This metal-free, facile reaction proceeds with atom economy under mild conditions with a broad range of secondary N-H amides, including benzanilide, acetanilide, oxindole, isatin, quinolinone, and maleimide, affording stable N- and O-acetals in excellent isolated yields. In addition, the chemoselective insertion reveals the robustness of this chemical transformation.

引用

页码：1727 / 1732

页数：6

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